Failing to Attach Pro Support Token

I've come across an issue when trying to enable the Ubuntu Pro Support Token(Paid Subscription):

:~$ sudo pro attach [Redacted][sudo] password for [Redacted]:Failed to attach machine. See https://ubuntu.com/pro/dashboard

Not very helpful, however when I run sudo pro attach without the Token:

:~$ sudo pro attachInitiating attach operation...Failed to access URL: https://contracts.canonical.com/v1/magic-attachCannot verify certificate of serverPlease check your openssl configuration.:~$ openssl versionOpenSSL 3.0.2 15 Mar 2022 (Library: OpenSSL 3.0.2 15 Mar 2022):~$ openssl version -dOPENSSLDIR: "/usr/lib/ssl"

Certs are indeed showing in that location.

:~$ curl -vs https://contracts.canonical.com*   Trying 185.125.190.31:443...* Connected to contracts.canonical.com (185.125.190.31) port 443 (#0)* ALPN, offering h2* ALPN, offering http/1.1*  CAfile: /etc/ssl/certs/ca-certificates.crt*  CApath: /etc/ssl/certs* TLSv1.0 (OUT), TLS header, Certificate Status (22):* TLSv1.3 (OUT), TLS handshake, Client hello (1):* TLSv1.2 (IN), TLS header, Certificate Status (22):* TLSv1.3 (IN), TLS handshake, Server hello (2):* TLSv1.2 (IN), TLS header, Finished (20):* TLSv1.2 (IN), TLS header, Supplemental data (23):* TLSv1.3 (IN), TLS handshake, Encrypted Extensions (8):* TLSv1.2 (IN), TLS header, Supplemental data (23):* TLSv1.3 (IN), TLS handshake, Certificate (11):* TLSv1.2 (OUT), TLS header, Unknown (21):* TLSv1.3 (OUT), TLS alert, unknown CA (560):* SSL certificate problem: self-signed certificate in certificate chain* Closing connection 0

At this point my only guess would be there is something wrong with the structure the certificate path. I have never seen the issue self-signed certificate in certificate chain. Any help or guidance would be greatly appreciated.